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A Sweetheart (sometimes heartsweet) is Chris's flavor-of-the-month. Chris's goal is to build a Sweetheart from the Ground-Up, lose his dreaded virginity (which he ultimately accomplished without a sweetheart), and spawn his God-chosen daughter, Crystal Weston Chandler (named after "the illustrious metal" and a name similar to his own). Unfortunately for him, the plan hasn't progressed beyond a handful of troll-engineered dates, a trip to a hooker (two in fact), and having sex with his mother. Thus the sweetheart label finds itself frivolously applied, indicating a status that lies somewhere between "e-girlfriend" and "stalking victim." Contrast this with Chris's Gal-Pals; that is, all of those girls who are still potential sweethearts because they are known to Chris and don't appear to hate him.

Chris's ideal vision for a sweetheart is more or less one that allowed him to continue living as a "self-employed" stay-at-home husband/father/son, since he didn't make a significant effort to support a prospective family at any point during his Love Quest aside from briefly applying for a minimum-wage job for Kacey. Based on his frustration at the idea of doing any work whatsoever, it's likely that he wanted someone to effectively mother him rather than an equal partner, who he could also have sex with and impregnate with a kid or two. Chris also seemed to be under the impression that they'd live with his parents and their hoard, who he'd presumably leave his sweetheart-to-be to raise his kids with.

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